


And Then There Were Three

by dugindeep (hotsauce)



Category: Supernatural
Genre: Blow Jobs, Consensual Underage Sex, Double Vaginal Penetration, F/M, M/M, Sibling Incest, Threesome - F/M/M, Vaginal Fingering, Vaginal Sex, Wincest - Freeform
Language: English
Status: Completed
Published: 2020-11-25
Updated: 2020-11-25
Packaged: 2021-03-09 22:26:50
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,392
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27713366
Author URL: https://archiveofourown.org/users/hotsauce/pseuds/dugindeep
Summary: Written for Fall 2020SPN_Masqueradefor the prompt:One night, Dean brings a girl back and as they’re getting hot and heavy he hears his brother’s tiny moans from masturbating in the bed nest to them. Sam is petrified, then the girl comes into his bed and Dean lies down beside them step-by-step tells Sam what to do ...
Relationships: Dean Winchester/Original Female Character(s), Dean Winchester/Sam Winchester, Dean Winchester/Sam Winchester/Original Female Character(s), Sam Winchester/Original Female Character(s)
Comments: 9
Kudos: 95
Collections: SPN_Masquerade Fall 2020





	And Then There Were Three

It's well past midnight when Dean slips back into the motel room with Katie wrapped around him.

He met the leggy blonde with the bubblegum-pink lips at the old-school 50’s diner across the street and he drank far too many coffees just for the sake of seeing her cute ass and big tits in the cheesy waitress dress. Then she started sneaking some whiskey in— _a lil irish coffee_ , she’d winked—and he couldn’t wait for her to get off for the night so he could … get off, too.

When she giggles, he puts a finger to her lips and she pulls back.

“Do we have to whisper?” she asks quietly.

“A little, yeah,” he replies just as softly, as he turns and brings her up against his body. He holds her face and kisses her, going for gentle to ease her into it.

Katie immediately jumps right in by shoving her tongue in his mouth and her hand down the front of his pants. It betrays the shy smiles and teasing pokes to his shoulder when she’d set each fresh cup of coffee down, but he’s glad to not have to do the hard work here. He’s not drunk- _drunk_ , but she was pretty heavy-handed with the alcohol so he’s ready to roll right with her and see where the night goes ...

She pushes him to the bed and he falls with a loud _hmph_ as she tumbles on top of him, which makes her laugh before Dean covers her mouth with a soft _shh_. Sitting across his waist, Katie reaches up for the ceiling, pressing her chest out and grinning down at him, her bright whites shining in the streetlamp slanting through the window. “You afraid we’ll get a noise complaint?” she teases as she rocks her ass down into his groin.

Dean groans and reaches up for her tits while quietly explaining that his dad is next door, probably passed out thanks to Jim Beam, and Sammy should be fast asleep under the covers.

_Should be_.

He glances at the other bed and sees a quick movement under the blankets. It stops as soon as Dean’s spent more than a few seconds watching the bed, and his eyes widen in horror that Sammy is moving. But then his mouth drops open with a bitten-off groan when Katie rests her hands on his chest and really grinds into him.

She shoves his flannel over his shoulders and pinches his nipples through his t-shirt, making him shiver, and he returns the favor to her. When he grabs her tits and squeezes her nipples, she gives a little squeal of delight. “Yes, fuck, twist ‘em,” she begs. When he does, she pushes down harder on his dick, so he does it again and again until they’ve quickly got a steady rhythm rubbing together.

He pulls the zipper of her top a few inches and gets a hand into the V of her dress and under a lacy bra to hold her tit in his palm. Right after, she pulls the zipper right down to her waist to give Dean more room to play, so he pulls her tit out then runs his other hand over her hip and down the back of her thigh to keep tugging her over his dick at a steady pace. He slides his hand right up the back of her dress and realizes she’s not wearing underwear, then he kicks his head back on the mattress and sends up a silent prayer of thanks to whatever god gave him this girl on this night.

She bites her lower lip and he reaches up to thumb it while he watches her tit shake out of the bra with every hitch of her hips. Her blond hair falls in waves around her face and her top is wide open with one breast poured out of the pale lacy bra. And when her plump lip catches in her lower lip, it all paints the perfect porn mag wet dream and he thinks he may come right in his jeans with just the picture.

Of course, that’s when everything falls apart.

Katie chuckles a little too loudly and before Dean can shush her, she calls out to the rest of the dark room. “Like what you see, kid?”

“What the—” Dean freezes and frantically looks around, half-expecting to see the ghost they’re in town to salt and burn coming for them, but no, it’s worse. It’s his little brother in the next bed, lit up by a semi passing by, with his fist furious under the covers and wide eyes trained right on them. “Fucking shit,” he grunts as he turns to the side and all but tosses Katie off of him and onto the floor.

Miraculously, she nails the landing and takes an airy hop between the beds until she’s on the other mattress and crawling over Sam like a sly cat.

Dean flips on the light between the beds, rights his open flannel into place, flapping the shirt tails over the tent in his jeans, and prepares to excuse it all away … but it seems like it’s Katie who has some explaining to do.

In the soft light of the room, Dean can see a high flush on Sam’s cheeks, Katie’s, too, and her lips are curled into a dangerous smile as she traps Sam in with a knee and hand planted on either side of him on the bed.

“Heya, honey,” she purrs. “You must be the little brother.” She turns to Dean, yet remains uncomfortably close to Sam, her free tit rubbing at Sam’s bare chest. “You didn’t say he was so damned cute.”

Sam keeps looking between kjati,and Dean doesn’t think he’s seen his brother so terrified. Not even when Dean took him on his first hunting trip or when he had Sam help patch up some nasty wounds that nearly tore Dad open along his hip.

“You wanna play with us, hon?” Katie asks Sam, drawing a finger down his nose.

The air is completely sucked from the room and Dean hears his heart thundering in his ears as he waits for Sam to answer, and his stomach spirals with heat when he realizes he’d really enjoy watching how this plays out. Dean subtly covers his hard on, squeezing it down, but his dick isn’t listening when he sees that Sam’s still got his own big one at attention under the covers.

Katie looks to Dean and her big white grin is warm and taunting all at once. “What do you think, Big D?”

He laughs, the sound breaking high as he recalls telling her all his good friends call him that. He even winked and she dared to blush as if it was improper … the hell was she blushing about when this is what she’s into?

Dean could blame her for dragging them to this moment, or he could blame the alcohol, but maybe there’s something else … Instead of shying away from it, Dean tips his head and smirks at his brother. Because just like the letters to Penthouse, this is a once in a million kind of deal at his feet.

“What do _you_ think, Sammy?”

At 15, Sam is still earnest and careful, keeps his head down unless asked for his opinion, so it shouldn’t be surprising that he doesn’t say anything. Sam just glances up at Katie still hovering right over his face, then over to Dean sitting on the bed just four feet away.

“Yeah, Sammy,” Katie sing-songs, drawing patterns with her fingertip on Sam’s flushed cheeks.

Sam makes a noise, a question, and Dean nods at him with a bit of cockiness and a whole lot of interest for how far Sam will follow along. “Go ahead, bro. You a breast man? Hers are nice and heavy.”

Slowly, Sam’s hand comes up to cup her free breast, just barely holding, but his eyes are right on it the whole time, so Dean figures the kid’s not totally spooked.

“Play with her nipples,” Dean encourages. “She really likes that.”

“Yeah, Sammy,” she whispers just before kissing the tip of his nose then sitting back in Sam’s lap.

Dean can see how she grinds down on Sam, right where his boner is, and knowing she’s got nothing between her and the covers … _fuck_ , Dean finds himself fondling his own dick at the thought of this beauty fucking his brother right in front of him.

It has to be the alcohol, right? Or this chick. Or this night. He isn’t about to question it when he and Sam look right at each other and he sees the lust blowing dark circles in Sam’s eyes.

“You wanna touch her some more?” Dean asks, voice dark and gravel.

“Yes,” she whines all wanton and high-pitched, “touch me, Sammy.”

Sam’s hands are tentative when they wrap around her hips and Dean chuckles, getting up to join them on the bed and help his brother out.

“Sit up a lil, sweetheart,” he says with a tap to Katie’s ass. Then to Sam, “Let’s see what you’re packing,” while pulling the blankets away. “Oh, _Samuel_ ,” he intones with some mock respect, because his little brother ain’t so little. That 15-year-old dick is at least the length of the kid’s already long palm and fingers and at least a half-dollar wide.

Katie leans down with her lips mere inches from Sam’s dick and hums rather happily, wanting. “Look at that.” She licks her top lip and looks right at him. “Can I taste you, honey?”

Sam stutters out a nod and Katie looks up at Dean.

“Touch me, D,” she orders, in direct contrast to the warm honey voice she gives Sam. Still, he listens, always ready to take orders. And he’s glad to do so because she moans when his hand drops over her ass and up the back of her skirt.

Dean finds her all wet and warm and his fingers easily slide along her lips and up to her clit. Her deep moans are muffled with her taking Sam into her mouth, but the noises hit Dean in the gut all the same and his dick aches in his jeans.

“You like what she’s doing?” Dean asks Sam. With his brother’s nod, still shaky yet quicker this time, Dean smiles with encouragement. “You want her to go faster, just ask her. You want her to do it harder, you ask.” When Katie groans at the suggestion, Dean rubs her pussy even harder. “You want him to tell you what to do?”

She pulls off Sam’s dick and huffs to catch her breath, stroking Sam with a loose fist and making the kid restless on the mattress. Grinding back on Dean’s fingers, Katie looks over her shoulder to him and he sees how her lips are even more plump and red than before, all because she was sucking his brother off right here, and he can’t help rubbing his dick through his jeans again.

“What do you want, sweetheart?” he asks Katie instead. “You want him to—”

“Both of you,” she murmurs.

Dean swears his stomach drops to his toes. It’s one thing to watch and get a little for himself, but _both_ sounds like a hell of a lot of lines to cross.

She arches her back, her ass curving up at a delicious angle with each rock of her body and forcing his fingers quicker through her wetness. “At the same time.”

“What?” Dean asks, air leaving him for a long moment.

“Gimme some of little Sammy and some of Big D.” Katie punctuates the point by tugging her lower lip between her teeth and letting it drag all the way out. “Together.”

“ _Shit_ ,” Sam mutters, his first word since Dean returned to the room.

It takes a few long moments of them staring at one another for Dean to figure out what this means … he’s the adult here, he should be the one to put a stop to this. At the very least, he shouldn’t make his brother do any of this if he’s not …

Katie looks back at Sam and overexaggerates her fist stroking up and down, her voice dragging low like the stirring in Dean’s gut. “You up for that, Sammy?” After a second, she giggles, cants her hips back onto Dean’s hand again. “Feels like you’re definitely _up_.”

Sam turns to Dean again and mouths his name, the room deathly quiet aside from the soft wet noises of his fingers against Katie’s folds and her fist on Sam.

“If you wanna,” Dean murmurs and Sam is nodding before the words are fully formed, so that settles it.

Needing a quick boost, Dean goes to his duffle, pulls out a flask, and takes a long swig. It burns down his throat and he forces a smile as he offers it to Sam, who shakes his head. Dean supposes if he had a hot chick in his bed at 15, he wouldn’t stop for anything.

Back at the bad, Dean smiles a bit deliriously and smacks Katie’s ass. “Alright, you better let Sammy get a feel for you.” He positions her further up Sam’s body and when he settles in behind her, he reaches around to pull her skirt up.

A quiet gasp leaves Sam’s mouth just as Katie lets out a giddy noise. Dean laughs, enjoying the little surprise for his brother. If they’re going to do this, then he’ll be sure to give Sam a first-class education.

With his chin over Katie’s shoulder, Dean nods at Sam and tells him, “Reach under there, between her legs. You gotta test drive it before you buy it.”

Sam is slow as molasses here, too, his fingers taking their time to disappear between her legs. Dean watches as she rolls her hips forward and down, and he gives his brother some affirmation then tells him to pull his fingers up through her folds.

When Katie shakes a little, Dean huffs with a smile. “There you go, kiddo. You found the clit right there.”

Those hazel eyes light up and Sam runs his fingers back and forth with Katie humming along with each touch. Dean frees her other tit and holds both in his hands, rolling them in his palm while she leans back into him.

Dean mouths at her ear and asks, “How’s my li’l bro doing, sweetheart?”

“Good, but I want more.”

He looks down at Sam and tips his head with a grin. “You heard the woman.” Sam’s hand quickens to Katie shaking in Dean’s arms and for all that Dean would love to feel her come and fall apart, it’s too early. He holds her back to him, hands tight around her tits, so she can’t fuck herself just yet. “Okay, Sammy, you ready for the real deal?”

Sam brings his hand down to the mattress and Dean sees how he tries to hide rubbing his hand on the sheets; it makes Dean chuckle. What a rookie. But he’s also glad for the quick break so he can go into his wallet and get a condom.

Dean walks Sam through every action to open the condom, roll it down his dick, “there you go, bud,” he praises, and then he brings Katie back into position. From over her shoulder, Dean can see Katie hold her skirt up with one hand, grab Sam’s dick with the other, then slide forward and sink down on it. She whimpers just as Sam groans, their voices cracking loud in the heated pressure of the room.

Katie hums for a few solid seconds as she stays seated on Sam, her hands coming up to grip Dean’s hands tighter around her tits. “Your little brother is so fucking big.”

Sam’s fingers twist in the sheets as his body tenses, trying to keep completely still. But Katie starts moving, swaying her hips back and forth in an easy rhythm and Dean bites at her neck while searching for any signs of worry on Sam’s face.

There are none, just bitten-lip bliss as Sam finally touches her again, first her knees then his fingers tip-toe up her thighs to hold on as she rides him. Sam pushes his head back into the pillows and whines up at the ceiling, and Dean grinds into her ass, plucks her nipples between his fingers, and watches the strain of thick muscles and veins in his brother’s neck.

“That’s real good, Sammy,” Dean assures him.

“ _Real_ good,” she agrees in between breaths punched out of her chest. “You’re doing real good.”

“I don’t wanna come yet,” Sam whines, pushing at Katie’s knees and she chuckles as she slows her hips.

“Well, good, honey, because I don’t want you to either.” She rises up from Sam’s lap and leans fully into Dean, leaning back to kiss his jaw. “You got another one of those rubbers for your Big D?”

Dean kisses her right on the mouth, digging in deep with his tongue as he rubs his dick at her ass. He pulls off with a big pop before he gets carried away and gets into action to grab what ends up being the last condom in his wallet—he looks up to the ceiling in thanks for that. It’s quick work to get his pants off, his flannel tossed in the corner, and his boxers down enough to get his dick out and covered. Then he’s slipping right inside her, all wet heat sucking him in, and his hips can’t hold back from going of their own volition to fuck her down to her hands and knees.

Katie’s face hangs right over Sam’s as she pants and whimpers with every hit of Dean deep inside until she gets down to her elbows, closer to Sam, and dives in to kiss him. Dean holds tight on her hips, pulling her back on his dick, and he watches her blond waves drape Sam’s head. Then she pulls back and bends into Dean’s hits, her hair a long curtain up Sam’s chest until she stretches languidly up towards the ceiling.

One of her arms wraps up and back around Dean’s neck and his hands fall down her thighs, suddenly bumping fingers that he realizes are Sam’s. He stutters through fucking her and looks at his brother, who’s eyes are probably as wide as Dean’s are, but they both yank their hands back into other places on her body.

“Big D,” Katie hums against his jaw, bringing him back to the moment. “So nice and big.”

Dean rubs his cheek to hers and smiles as he continues rocking into her. “Thanks, sweetheart. You’re one in a million, too.”

“But I want Sammy, too.”

It’s a quick hit to Dean’s ego and he stops in place, which actually helps Katie because she reaches down for Sam’s dick and lines it up with where Dean is already deep inside.

“C’mon now, you can do it,” Katie teases like a school teacher coaching a nervous student.

And maybe that’s exactly what Dean’s tied up in here, because he’s frozen in place and she gets the job done by nudging Sam in right alongside Dean. It takes a hell of a long time, probably made longer as Dean holds his breath, because he’s sure he’ll wake up any minute now in some other motel room, by himself in bed, or maybe in Hell, because this is definitely not something he should be doing with his brother.

“ _Oh_ ,” she huffs out when she’s got them right where she wants. Then as she adjusts and tests a rock of her hips, her smile is obvious when she says, “There we go, boys.”

Dean watches as she moves down with her hands on the mattress and glances over her shoulder to wink at him.

When she turns back to Sam, she murmurs, “You ready, Sammy?”

Sam tests it out with a little move then Dean feels the drag of his brother’s dick on his and there are all sorts of sensations flaring in his body. As Sam keeps going with small shifts of his hips, Dean is stuck in place, his head screaming to leave this situation because all he’s supposed to do in life is protect his brother and instead, he’s corrupting him.

But then Katie moans and her cunt trembles around them and Dean’s other brain kicks in, wanting immediate relief. He’s already fully enveloped with heated skin and his dick aches, so the only logical thing is to start fucking into Katie at the same pace as his brother.

She huffs out on each push in and Dean fondles one of her tits, twisting the nipple to make her cry out every so often, and he brings his other hand down to cup her pussy. All their noises melt together—Sam panting loud and wet, Katie’s whiny whimpers echoing off the walls, and Dean grunting with every roll of his body. And Dean keeps on playing with her clit, running fingers along the sides, tugging underneath, and sliding even further back towards her pussy. That’s when he feels the base of Sam’s dick and jerks his hand back.

Sam groans and clenches his eyes shut.

“You okay, Sammy?” Dean asks, yet holds his breath in case his brother is very much not.

A nod is the only answer.

“You’re doing good, bro.” Dean pants in between words and smiles at Sam. “Right, honey? My brother’s doing you good?”

“So good,” she breathes out. “I’m so full. Love being stuffed with you boys.”

Sam groans again and Dean’s sure the kid’s reactions are more about Katie’s pussy giving him a hell of a good night, so he shakes off the worry and goes back to fingering at her. When he again bumps Sam’s dick, Sam whines like before with his hips canting up quickly before dropping back into the regular pace they’ve set.

Dean chases after the feel of Katie squeezing on their dicks and he keeps rubbing at her clit and back further, and every time he slips too far and touches Sam, his brother cries out. The sound pounds through Dean’s chest and then he finds himself fucking faster and sliding his fingers in long strides through Katie’s wetness and along Sam’s dick with more intent as he watches his brother fall apart.

Finally, Dean sees the tick of Sam’s jaw, the grit of his teeth, and the tight lines in his forehead as his little brother comes with guttural moaning and full-body trembles.

“Thatta boy, Sammy. Good for you.”

Sam smiles a little and Dean keeps his eyes on his brother as he pulls Katie off Sam’s dick and into his own lap so he can fuck her through the end of this. He wants to be sure when Sam’s eyes finally open, they’re not filled with fear or regret, and suddenly he thinks he may also want Sam to see him get this girl off.

Dean yanks her skirt up high and plays at her clit with the fingers on both hands as she bounces in his lap. She cries out as she breaks and Sam finally looks up to her and Dean. His whole face is red with exertion and exhaustion, his hazel eyes dark and heavy as he loosely strokes himself with the last shudders of his body

Their eyes are right on each other as Dean fucks Katie through her orgasm, her pussy squeezing at him just before he finally comes with a shout.

Katie falls onto the bed with a satisfied sigh and Dean laughs, drained yet elated. As he pulls his condom off and ties it, he sees Sam following suit and he smirks. At least he doesn’t have to teach his brother that.

The condoms are tossed near the garbage to be handled later. Dean drops to the mattress between Katie and Sam, bringing his arm up above his brother’s head on the pillow and grinning at Katie. “Well, that was certainly more than I bargained for.”

She grins back and rolls into him. “Me, too, Big D.” She kisses him deep and dirty real quick before popping off the bed to stand. Seconds later, she’s in the bathroom, obviously taking a piss with the door open, but Dean supposes there isn’t much for privacy after what they just did.

Once back in the room, she zips her top back up, grabs her purse off the ground, and heads for the door.

Dean sits up a little. “Wham, bam, thank you, ma’am?”

“Aww,” she coos with a put-upon smile, “Are you a cuddler?”

“No, I just—” He clears his throat, ignoring the hit to his ego that she’s lost some of her shine in the afterglow.

“I work a double tomorrow,” she explains with a frown. “Gotta be up early.”

Dean nods, letting her get on with the excuse. It’s not like he planned to bring her home to Dad or put a ring on her finger or anything. He feels Sam lean in at his side and he figures he’ll have to talk to Sam about one-night stands and leaving women in every town, if they don’t leave first.

Katie winks, but it seems like it sails right past Dean to Sam. “You boys know where to find me.” She flits a little finger wave and Sam does the same with a shy _see ya_ and drops his hand on Dean’s chest.

Then she’s gone and the door slams shut, leaving them to the vacant quiet of whatever comes next.

After a calming sigh, Dean falls back in bed and Sam is still at his side, arm strung across Dean’s chest. His fingers dance along Dean’s ribcage, tickle a little, but Dean restrains from moving.

He has to force a solid front as his body holds firm and he ignores any alarm bells firing deep inside. Instead, he scruffs the back of Sam’s head, kisses the top of his brown mop of hair, then turns towards the rest of the empty room to sleep.

When that slim hand falls to the center of Dean’s chest, Dean doesn’t move it. And when Sam’s palm presses into it, Dean smiles a little and lets himself finally sink into the bed and sleep.


End file.
